My 3-year-old son, soon to be 4, is obsessed with wearing dresses. He
has been interested in dresses since he could talk. We are an
open-minded family. We do not spank and have a family bed. At first, I
thought he just wanted to be like his older sister and I. but now he
wants to wear them all the time. It is very painful for him to be denied
this. His crying when refused his wish to where a dress is sincere and
breaks my heart. I am a stay at home Mom. I would like to hear from you.
I do not want to hurt, or interfere with my son's true identity. Please
help.

Name Withheld

Jan's reply:

Hi,

Thank you for visiting our Natural Child Project site and for sending
in this interesting and challenging question.

While your son's behavior would probably worry any parent, my first
piece of advice is not to jump to conclusions. There is a philosophical
tool called "Occam's Razor" which urges us to select the
simplest solution to a problem. In this circumstance, such a tool is
very relevant.

When a child shows a preference that seems to imply some sort of
sexual aberration according to our cultural values, the danger is that
we may inadvertently cause the very thing we fear if we react with
anxiety, however understandable that may be. As I'm sure you know,
children can pick up on anxious feelings even when they are not
expressed directly.

Instead of demonstrating anything to do with sexuality or gender
roles, your son may have something much more simple in mind. He may find
dresses more comfortable than the pants he has worn. Perhaps his pants
are too tight? Is the fabric uncomfortable? Does he get a skin rash when
wearing certain fabrics? Does he find it easier to use the potty when
wearing a dress? And so on.

Or his behavior may have more to do with expressing resistance in
general. Has the family gone through some stressful times recently, that
he had no control over? Has his sister started school this month? Or are
there other kinds of circumstances that have made him feel a bit
helpless? This may simply be his way of establishing some control where
he can. Perhaps if some attention is given to minimizing frustration in
other areas, that may be helpful. I'm glad to hear that you are not
punishing, as that would certainly escalate the situation.

Your comment about his relationship to his sister and to you showed
great insight. If you are a single mother, or if you have a partner who
is gone most of the day, your son may simply be frustrated that he is
being asked not to model the two persons he spends the most time with.
If he could have more time with his father or another male, he may begin
to recognize why he is being asked to dress differently from you and his
sister.

I asked a colleague, Denise Green, for suggestions, and she asked if
you might find a compromise, such as a kilt or other ethnic type of
dress. She makes an interesting point here, because skirts and robes are
worn by men in many different world cultures, and your son is young
enough to still have some flexibility in dress codes. It's the culture
that is strange, after all: girls can wear pants, but boys can't wear
dresses. Perhaps your son is simply ahead of his time, or perhaps, like
many other children, he likes wearing costumes as a way to understand
what it's like to be a different person. Have you looked into acting
classes, where he could wear many different types of clothing in a
socially accepted way?

Denise also offers this advice: "The only thing I would suggest
that you didn't include, would be that she (and her partner if she has
one) might want to do some serious talking about how far she/they feel
comfortable allowing their son to indulge a counter-cultural dress
style. In order to deal with this without sending mixed messages to the
child, it will be important for the parents to find a solution that is
not too far outside either of their "comfort zones". Depending
on the family, that could be anything from allowing their son free rein,
to allowing dresses at home but requiring pants in public, to getting a
kilt or something similar, to requiring pants but doing a lot of
listening, comforting and allowing him to have his feelings of anger and
disappointment. I think, especially in a situation like this where there
is no clear-cut answer, that it's more important for the parents to be
clear and empathic than to choose a particular course of action."